To contribute to contemporary debates about the human self, historical constitutedness and capacity for critical agency, I turn to Niccolo Machiavelli's account of human virtuosity. There I retrieve a vision of political action that centres on a critically conscious intelligence or 'I' engaged in the continual fracturing and manipulation of identity. Machiavelli shows this critical intelligence to be something developed by way of a mental standpoint I call critical in-betweenness -- a disposition that imperfectly enables positive political innovation. To account for what proves to be a non-modernist Machiavellian view of a multiplicitous and capacious self, I turn to one of Machiavelli's ancient influences, Cicero, and his theory of four personae. I then further illuminate such virtuoso capacities for political innovation by way of a case study, Elizabeth Tudor of England. Finally, I briefly link this discussion to late/post-modern political and social theory, and to issues of democratic citizenship and education.
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